Former National Security Advisor John Bolton warned against renewed negotiations with Iran and criticized the Trump administration’s overture to Syria in a wide-ranging interview on Chicago’s Morning Answer with Dan Proft and Amy Jacobson.
As President Trump wrapped up a high-profile visit to Saudi Arabia and touched down in Qatar, Bolton emphasized that diplomacy with Iran’s regime is not only futile but counterproductive. Trump’s recent comments—offering Iran a chance to strike a new nuclear deal while also vowing to impose “maximum pressure” if they refuse—struck Bolton as dangerously optimistic.
Bolton: Iran Is Stalling for Time
“There’s no evidence Iran has abandoned its objective of getting deliverable nuclear weapons,” Bolton said flatly. He argued the regime is reeling from Israeli attacks on its missile infrastructure and setbacks suffered by its proxies Hamas and Hezbollah—but that doesn’t mean they’re ready to give up their nuclear ambitions.
In Bolton’s view, Tehran would love nothing more than a prolonged negotiation to buy time and shield what’s left of its weapons program. He warned that some in the Trump administration may be getting duped by seasoned Iranian negotiators.
“If there’s any hint that Trump is about to agree to a deal like the Obama deal, the political backlash would be enormous,” Bolton said. “That was the central flaw in 2015—allowing uranium enrichment. It should never have been allowed.”
Calls Deal-Making With Damascus Premature and Risky
Bolton also cast doubt on the decision to lift sanctions on Syria and normalize relations with President al-Sharah, a former al-Qaeda affiliate now styled as a reformed national leader.
While acknowledging that Syria’s break from Iran is a positive geopolitical shift, Bolton said reestablishing diplomatic ties should come with hard conditions.
At the top of Bolton’s list: full transparency about the Assad regime’s chemical and biological weapons, the release of information on past hostage takings, and a renunciation of terrorism. He even suggested the Syrian regime demand that Russia vacate its military bases as a signal of independence.
“I don’t want just rhetoric from this new regime. I’d like to see performance,” Bolton stated.
Cautions Against Accepting Qatar’s Dreamliner for Trump
The former national security advisor also weighed in on Qatar’s controversial offer of a customized 747 Dreamliner for Trump’s use as a temporary Air Force One—an offer that has raised eyebrows even among Trump allies like Senator Rand Paul and commentator Lara Loomer.
Bolton questioned the security implications of accepting a previously used aircraft, citing the sophisticated defense and communications technology built into Air Force One.
“It’s a flying office, not a luxury aircraft,” Bolton noted. “Operationally, you don’t want a plane that’s been in someone else’s hands for years. That’s a big risk.”
A Cautious Tone on Trump’s Middle East Strategy
Although Bolton helped Trump pull out of the Obama-era Iran nuclear deal in 2018, he appears increasingly concerned that the administration may be drifting back toward conciliatory positions—either out of political expediency or misplaced confidence in diplomacy.
He acknowledged Trump’s previous success in applying economic pressure, particularly in cutting off Iranian funding to terrorist groups, but warned against misjudging the regime’s intentions.
“If he means this as an ultimatum, he needs to follow through—otherwise, it’s a signal of weakness.”
As tensions in the Middle East continue to simmer, Bolton’s remarks serve as a reminder of the stark divide between those seeking strategic accommodation and those, like Bolton, who believe the only effective strategy against authoritarian regimes is pressure without compromise.
John Bolton is the former Assistant to the President for National Security Affairs and the author of The Room Where It Happened: A White House Memoir.